2-oxo-1-imidazolidinyl imidazothiadiazole derivatives

1. A compound having formula (I), or a geometrical isomers, enantiomers, diastereomers, isotopes or mixtures thereof, or a pharmaceutically acceptable salt thereof,

wherein

R 1 is a C 1-4 alkyl optionally substituted by one or more halogen substituents;

R 2 is a C 1-4 alkyl substituted by an alkoxy substituent.

2. A compound according to claim 1 , wherein R 1 is an i-butyl, a n-propyl, a 2,2-difluoropropyl, a 2-chloro-2,2-difluoroethyl, a 2,2-difluoroethyl, a 2,2,2-trifluoroethyl, or a 2-fluoroethyl moiety.

3. A compound according to claim 1 , wherein R 1 is n-propyl, a 2-chloro-2,2-difluoroethyl, a 2,2-difluoropropyl or a 2,2,2-trifluoroethyl moiety.

4. A compound according to claim 1 , wherein R 2 is a methoxymethyl, a [( 2 H 3 )methyloxy]methyl, a methoxy( 2 H 2 )methyl, or a [( 2 H 3 )methyloxy]( 2 H 2 )methyl moiety.

5. A compound according to claim 1 , wherein:

R 1 is a n-propyl or a 2,2,2-trifluoroethyl moiety;

R 2 is a methoxymethyl, a methoxy( 2 H 2 )methyl, a [( 2 H 3 )methyloxy]methylor a [( 2 H 3 )methyloxy]( 2 H 2 )methyl moiety.

6. A compound according to claim 1 which is:

(4S)-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one;

(4R)-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]ethyl]-4-propyl-imidazolidin-2-one;

(+)-4-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)imidazolidin-2-one;

(−)-4-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)imidazolidin-2-one;

(4S)-1-[[2-[dideuterio(trideuteriomethoxy)methyl]-6-(difluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one;

(4R)-1-[[2-[dideuterio(trideuteriomethoxy)methyl]-6-(difluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one;

(4S)-1-[[2-[dideuterio(methoxy)methyl]-6-(difluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one;

(4R)-1-[[2-[dideuterio(methoxy)methyl]-6-(difluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one;

(−)-4-(2-chloro-2,2-difluoro-ethyl)-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]imidazolidin-2-one;

(+)-4-(2-chloro-2,2-difluoro-ethyl)-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]imidazolidin-2-one;

(+)-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2-difluoropropyl)imidazolidin-2-one;

(−) 1-[[6-(difluorornethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2-difluoropropyl)imidazolidin-2-one;

(+)-5,5-dideuterio-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one; or

(−)-5,5-dideuterio-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-propyl-imidazolidin-2-one.

7. A pharmaceutical composition comprising an effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable diluent or carrier.

8. A method for the treatment of epilepsy, epileptogenesis, seizure disorders, or convulsions, comprising administering to a patient in need thereof an effective amount of a compound or salt according to claim 1 .

9. A method according to claim 8 , wherein the treatment is for refractory seizures.

10. A compound according to claim 2 , wherein R 2 is a methoxymethyl, a [( 2 H 3 )methyloxy]methyl, a methoxy( 2 H 2 )methyl, or a [( 2 H 3 )methyloxy]( 2 H 2 )methyl moiety.

11. A compound according to claim 4 , wherein:

R 1 is a n-propyl or a 2,2,2-trifluoroethyl moiety;

R 2 is a methoxymethyl, a methoxy( 2 H 2 )methyl, a [( 2 H 3 )methyloxy]methylor a [( 2 H 3 )methyloxy]( 2 H 2 )methyl moiety.